Triethylamine → HCID 32676578, compound

HRID 1486818Notes

Reaction equation

HRID 1486818 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=O)=[N:9][CH:10]=1)=[O:4].[CH:14]1([NH2:17])[CH2:16][CH2:15]1.CCN(CC)CC.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH:14]1([NH:17][C:11]([C:8]2[N:9]=[CH:10][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:6][CH:7]=2)=[O:13])[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 69828CyclopropylamineHCID 3149925-(Methoxycarbonyl)pyridine-2-carboxylic acidHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 32676578HCID 32676578, compoundYield 42.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-(Methoxycarbonyl)pyridine-2-carboxylic acid (1.50 g, 8.28 mmol) was dissolved in DMF (25 mL) and cyclopropylamine (689 uL, 9.94 mmol), Et3N (4.66 mL, 33.1 mmol) and HBTU (3.30 g, 8.69 mmol) were added. The reaction mixture was stirred for 3d and concentrated in vacuo. The residue was dissolved in EtOAc (100 mL), washed with sat aq Na2CO3 (100 mL), dried (MgSO4) and concentrated in vacuo. The residue was purified by column chromatography to give the title compound (774 mg, 42.4%) as a white solid. LCMS (ES+): 221.2 [MH]+.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in EtOAc (100 mL)
  3. washwashed
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0fede0997c2548be9e5b940c82f6d35b
Source dataset
uspto-grants-2016_08
Patent number
US09428498B2

Reaction notes

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